SN2 Ring Opening of β-Lactones: An Alternative to Catalytic Asymmetric Conjugate Additions
- 29 May 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (14) , 4680-4683
- https://doi.org/10.1021/jo025519n
Abstract
Merging catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions with ensuing Grignard-mediated ring opening of the derived enantiomerically enriched β-lactones is presented as a generally useful asymmetric synthesis of β-disubstituted carboxylic acids. Enantiomerically enriched β-lactones are subject to efficient SN2 ring opening with a variety of copper-modified alkyl Grignard reagents, including highly branched nucleophiles. Considerable structural variation in the lactone electrophile is also tolerated. Phenyl- and vinyl-derived organometallics are not efficient nucleophiles for the ring-opening reactions.Keywords
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